This invention relates to N-[(heterocyclic)(alkyl)aminocarbonyl]benzenesulfonamides useful as agricultural chemicals.
In EPO Publication 0023422, published Feb. 4, 1981, the following compounds are taught to be herbicides, especially useful for controlling weeds in wheat. ##STR1## wherein W is O or S;
R is CHF.sub.2, CF.sub.3, CH.sub.2 CF.sub.3 or CF.sub.2 CHFG, where G is F, Cl, CF.sub.3 or Br; PA1 A is O or S(O).sub.n, where n is 0, 1 or 2; PA1 R.sup.1 is H, F, Cl, Br or CH.sub.3 ; PA1 X is CH.sub.3 or OCH.sub.3 ; PA1 Y is CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, (CH.sub.2).sub.m OCH.sub.3 (where m is 1 or 2), OCH.sub.2 CH.sub.2 OCH.sub.3, or OCHR.sup.2 CO.sub.2 R.sup.3, where R.sup.2 is H or CH.sub.3 and R.sup.3 is CH.sub.3 or C.sub.2 H.sub.5 ; and PA1 E is CH or N. PA1 R.sub.2 is H or alkyl of one to three carbon atoms; PA1 R.sub.3 is ##STR3## R.sub.4 and R.sub.7 are independently hydrogen, fluorine, chlorine, bromine, alkyl of 1-4 carbon atoms, alkoxy of 1-4 carbon atoms, nitro, CF.sub.3, CH.sub.3 S-- or CH.sub.3 CH.sub.2 S--; PA1 R.sub.5, R.sub.6 and R.sub.8 are independently hydrogen, fluorine, chlorine, bromine or methyl; PA1 X is Cl, CH.sub.3, --CH.sub.2 CH.sub.3, alkoxy of one to three carbons, CF.sub.3, CH.sub.3 S--, CH.sub.3 OCH.sub.2 -- or CH.sub.3 OCH.sub.2 CH.sub.2 O--; PA1 Y is CH.sub.3 or OCH.sub.3 ; and PA1 Z is CH or N; PA1 (a) R.sub.1 and R.sub.2 may not simultaneously be hydrogen; PA1 (b) when R.sub.4 and R.sub.8 are both hydrogen, at least one of R.sub.5, R.sub.6 or R.sub.7 must be hydrogen; PA1 (c) when R.sub.6 is other than H, at least one of R.sub.4, R.sub.5, R.sub.7 and R.sub.8 is other than H and at least two of R.sub.4, R.sub.5, R.sub.7 and R.sub.8 must be hydrogen; and PA1 (d) when R.sub.6 is H and all of R.sub.4, R.sub.5, R.sub.7 and R.sub.8 are other than H, then all of R.sub.4, R.sub.5, R.sub.7 and R.sub.8 must be either Cl or CH.sub.3. PA1 R is C.sub.1 -C.sub.4 alkyl substituted with 1-6 halogen atoms selected from 1-6 F, 0-3 Cl or 0-1 Br; PA1 R.sub.1 is H, F, Cl, Br, CH.sub.3, CF.sub.3 or OCH.sub.3 ; PA1 n is 0, 1 or 2; PA1 X is CH.sub.3 or OCH.sub.3 ; PA1 Y is CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, CH.sub.2 CH.sub.3, CH.sub.2 OCH.sub.3 or CH.sub.2 CH.sub.2 OCH.sub.3 ; and PA1 Z is CH or N; and PA1 (1) Compounds of Formula I where R is CHF.sub.2, CF.sub.3, CH.sub.2 CF.sub.3, CF.sub.2 CF.sub.2 H, CF.sub.2 CFHCl, CF.sub.2 CFHBr, CF.sub.2 CF.sub.3 or CF.sub.2 CHFCF.sub.3. PA1 (2) Compounds of Preferred 1 where R.sub.1 is H. PA1 (3) Compounds of Preferred 2 where R is CF.sub.3, CHF.sub.2, CH.sub.2 CF.sub.3 or CF.sub.2 CF.sub.2 H. PA1 (4) Compounds of Preferred 3 where A is O or S and Y is CH.sub.3 or OCH.sub.3. PA1 .cndot. N-[N-(4-methoxy-6-methylpyrimidin-2-yl)-N-methylaminocarbonyl]-2-(difluoro methoxy)benzenesulfonamide; PA1 .cndot. N-[N-(4,6-dimethoxypyrimidin-2-yl)-N-methylaminocarbonyl]-2-(difluorometho xy)benzenesulfonamide; PA1 .cndot. N-[N-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-N-methylaminocarbonyl]-2-(dif luoromethoxy)benzenesulfonamide; PA1 .cndot. N-[N-(4,6-dimethoxy-1,3,5-triazin-2-yl)-N-methylaminocarbonyl]-2-(difluoro methoxy)benzenesulfonamide; PA1 .cndot. N-[N-(4-methoxy-6-methylpyrimidin-2-yl)-N-methylaminocarbonyl]-2-(difluoro methylthio)benzenesulfonamide; PA1 .cndot. N-[N-(4,6-dimethoxypyrimidin-2-yl)-N-methylaminocarbonyl]-2-(difluoromethy lthio)benzenesulfonamide; PA1 .cndot. N-[N-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-N-methylaminocarbonyl]-2-(dif luoromethylthio)benzenesulfonamide; PA1 .cndot. N-[N-(4,6-dimethoxy-1,3,5-triazin-2-yl)-N-methylaminocarbonyl]-2-(difluoro methylthio)benzenesulfonamide; and PA1 .cndot. N-[N-(4,6-dimethoxy-1,3,5-triazin-2-yl)-N-methylaminocarbonyl]-2-(trifluor omethylthio)benzenesulfonamide. PA1 Z is CH; PA1 3.22s, N-CH.sub.3 ; PA1 4.08S, (OCH.sub.3).sub.2 ; PA1 6.56s, CF.sub.2 H; and PA1 7.2-8.2 mult., aryl; PA1 C=Chlorosis or necrosis; PA1 E=emergence inhibition; PA1 G=growth retardation; and PA1 H=formative effects.
In U.S. Pat. No. 4,257,802, issued Mar. 24, 1981, the following compounds are taught to be herbicides and plant-growth-regulants. ##STR2## wherein R.sub.1 is H, alkyl of one to three carbon atoms or --OCH.sub.3 ;
and their agriculturally suitable salts; provided that:
Compounds of Formula (ii), and their use as antidiabetic agents, are reported in J. Drug. Res. 6, 123 (1974): ##STR4##
The presence of undesired vegetation causes substantial damage to useful crops, especially agricultural products that satisfy man's basic food needs, such as soybeans, wheat and the like. The current population explosion and concomitant world food shortage demand improvements in the efficiency of producing these crops. Prevention or minimizing the loss of a portion of such valuable crops by killing, or inhibiting the growth of undesired vegetation is one way of improving this efficiency.
A wide variety of materials useful for killing or inhibiting (controlling) the growth of undesired vegetation is available; such materials are commonly referred to as herbicides. The need exists, however, for still more effective herbicides that destroy or retard weeds without causing significant damage to useful crops.